2-Chloroethyl isocyanate → 1-But-3-ynyl-3-(2-chloro-ethyl)-urea

HRID 1965960Notes

Reaction equation

HRID 1965960 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]=[C:5]=[O:6].[CH2:7]([NH2:11])[CH2:8][C:9]#[CH:10]>C(OCC)C>[CH2:7]([NH:11][C:5]([NH:4][CH2:3][CH2:2][Cl:1])=[O:6])[CH2:8][C:9]#[CH:10]

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 10034574But-3-yn-1-amine

Product 1

HCID 597873661-But-3-ynyl-3-(2-chloro-ethyl)-ureaYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add chloroethyl isocyanate (5.25 g, 50 mmol) dropwise to a solution of but3-ynyl-amine (3.4 g, 50 mmol) (prepared by following the procedure described in Tetrahedron Lett. 1987, 43, 5145) in ethyl ether (100 mL). Stir the suspension for 30 min and filter the solid to obtain the desired intermediate (8.7 g, 100%).

Workup

  1. customprepared
  2. filtrationfilter the solid

Sources & evidence

ORD record
ord-7a5f8d6b5fc64492901a3aff656875a6
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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